# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_moc148
_database_code_depnum_ccdc_archive 'CCDC 2239928'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;Faculty of Chemistry and Chemical Technology University of Ljubljana
Slovenia
;
_audit_update_record             
;
2023-02-05 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N6 O2'
_chemical_formula_sum            'C14 H20 N6 O2'
_chemical_formula_weight         304.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0049(7)
_cell_length_b                   10.5291(8)
_cell_length_c                   9.2006(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.405(10)
_cell_angle_gamma                90
_cell_volume                     743.90(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.8260
_cell_measurement_theta_min      3.5290

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            3676
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.652
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1701
_reflns_number_gt                1321
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.1440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1701
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30727(13) 0.98754(9) 0.05493(12) 0.0282(3) Uani 1 1 d . . . . .
N1 N -0.10452(16) 0.75763(12) 0.16582(15) 0.0304(3) Uani 1 1 d . . . . .
N2 N 0.11245(15) 0.67790(11) 0.08920(13) 0.0233(3) Uani 1 1 d . . . . .
N3 N 0.55219(15) 0.86470(11) 0.11859(13) 0.0238(3) Uani 1 1 d . . . . .
H3 H 0.659(2) 0.8552(15) 0.1082(17) 0.029 Uiso 1 1 d . U . . .
C1 C 0.01140(18) 0.77984(14) 0.09193(17) 0.0269(3) Uani 1 1 d . . . . .
H1 H 0.022585 0.858860 0.045714 0.032 Uiso 1 1 calc R U . . .
C2 C -0.07512(19) 0.63302(14) 0.21351(16) 0.0274(3) Uani 1 1 d . . . . .
H2 H -0.138847 0.588709 0.270378 0.033 Uiso 1 1 calc R U . . .
C3 C 0.05739(18) 0.58315(14) 0.16765(16) 0.0261(3) Uani 1 1 d . . . . .
H3A H 0.103131 0.499542 0.185968 0.031 Uiso 1 1 calc R U . . .
C4 C 0.24912(18) 0.66749(14) 0.01239(16) 0.0253(3) Uani 1 1 d . . . . .
H4A H 0.248001 0.744531 -0.049570 0.030 Uiso 1 1 calc R U . . .
H4B H 0.224760 0.593407 -0.056657 0.030 Uiso 1 1 calc R U . . .
C5 C 0.42875(19) 0.65233(13) 0.12482(17) 0.0271(3) Uani 1 1 d . . . . .
H5A H 0.423609 0.584099 0.197479 0.032 Uiso 1 1 calc R U . . .
H5B H 0.512065 0.625425 0.069176 0.032 Uiso 1 1 calc R U . . .
C6 C 0.49626(19) 0.77265(14) 0.21254(16) 0.0265(3) Uani 1 1 d . . . . .
H6A H 0.403221 0.810319 0.250420 0.032 Uiso 1 1 calc R U . . .
H6B H 0.595450 0.751350 0.301189 0.032 Uiso 1 1 calc R U . . .
C7 C 0.45446(18) 0.96022(13) 0.04759(16) 0.0227(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0215(5) 0.0287(6) 0.0379(6) 0.0007(4) 0.0141(4) 0.0001(4)
N1 0.0232(6) 0.0331(7) 0.0366(7) 0.0041(6) 0.0112(5) 0.0013(5)
N2 0.0197(6) 0.0247(6) 0.0260(6) 0.0019(5) 0.0073(5) -0.0029(5)
N3 0.0187(6) 0.0255(6) 0.0295(6) -0.0008(5) 0.0107(5) -0.0023(5)
C1 0.0228(7) 0.0260(7) 0.0323(8) 0.0050(6) 0.0083(6) 0.0009(6)
C2 0.0234(7) 0.0314(8) 0.0277(7) 0.0023(6) 0.0075(6) -0.0051(6)
C3 0.0248(7) 0.0249(7) 0.0285(7) 0.0030(6) 0.0072(6) -0.0038(6)
C4 0.0226(7) 0.0265(7) 0.0295(7) -0.0017(6) 0.0116(6) -0.0033(6)
C5 0.0242(7) 0.0242(7) 0.0350(8) 0.0060(6) 0.0119(6) 0.0020(6)
C6 0.0224(7) 0.0328(8) 0.0256(7) 0.0043(6) 0.0087(6) -0.0012(6)
C7 0.0210(7) 0.0227(7) 0.0264(7) -0.0061(6) 0.0097(6) -0.0037(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2330(16) . ?
N1 C1 1.3168(18) . ?
N1 C2 1.3824(19) . ?
N2 C1 1.3485(18) . ?
N2 C3 1.3749(17) . ?
N2 C4 1.4646(17) . ?
N3 C7 1.3273(18) . ?
N3 C6 1.4511(18) . ?
N3 H3 0.891(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.353(2) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9500 . ?
C4 C5 1.524(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.517(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C7 1.537(3) 3_675 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 104.53(12) . . ?
C1 N2 C3 106.55(11) . . ?
C1 N2 C4 127.03(12) . . ?
C3 N2 C4 126.36(12) . . ?
C7 N3 C6 124.13(12) . . ?
C7 N3 H3 118.8(10) . . ?
C6 N3 H3 117.1(10) . . ?
N1 C1 N2 112.46(12) . . ?
N1 C1 H1 123.8 . . ?
N2 C1 H1 123.8 . . ?
C3 C2 N1 110.33(12) . . ?
C3 C2 H2 124.8 . . ?
N1 C2 H2 124.8 . . ?
C2 C3 N2 106.12(12) . . ?
C2 C3 H3A 126.9 . . ?
N2 C3 H3A 126.9 . . ?
N2 C4 C5 111.74(11) . . ?
N2 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 113.55(12) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N3 C6 C5 111.37(11) . . ?
N3 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O1 C7 N3 126.11(13) . . ?
O1 C7 C7 121.24(16) . 3_675 ?
N3 C7 C7 112.64(14) . 3_675 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 0.06(17) . . . . ?
C3 N2 C1 N1 -0.15(17) . . . . ?
C4 N2 C1 N1 177.40(13) . . . . ?
C1 N1 C2 C3 0.06(17) . . . . ?
N1 C2 C3 N2 -0.15(17) . . . . ?
C1 N2 C3 C2 0.18(15) . . . . ?
C4 N2 C3 C2 -177.40(12) . . . . ?
C1 N2 C4 C5 114.17(15) . . . . ?
C3 N2 C4 C5 -68.75(17) . . . . ?
N2 C4 C5 C6 -71.88(15) . . . . ?
C7 N3 C6 C5 97.05(16) . . . . ?
C4 C5 C6 N3 -74.42(15) . . . . ?
C6 N3 C7 O1 2.8(2) . . . . ?
C6 N3 C7 C7 -178.18(13) . . . 3_675 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 N1 0.891(16) 2.088(16) 2.8874(17) 148.9(14) 1_655 yes
C2 H2 O1 0.95 2.60 3.5462(17) 174.0 2_545 yes

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042

_shelx_res_file                  
;
TITL moc148 in P21/c #14
    moc148.res
    created by SHELXL-2018/3 at 16:16:43 on 23-Mar-2021
CELL 0.71073 8.0049 10.52913 9.200575 90 106.4048 90
ZERR 2 0.000692 0.000767 0.000815 0 0.0096 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 28 40 12 4
EQIV $1 1+X,+Y,+Z
EQIV $2 -X,-0.5+Y,0.5-Z

L.S. 10
PLAN  20
SIZE 0.6 0.4 0.2
TEMP -123
HTAB N3 N1_$1
HTAB C2 O1_$2
CONF
BOND $H
fmap 2
acta
SHEL 20.4 0.77
REM <olex2.extras>
REM <HklSrc "%.\\moc148.hkl">
REM </olex2.extras>

WGHT    0.040100    0.144000
EXTI    0.017502
FVAR       9.07920
O1    4    0.307273    0.987538    0.054928    11.00000    0.02149    0.02870 =
         0.03788    0.00066    0.01407    0.00008
N1    3   -0.104516    0.757628    0.165815    11.00000    0.02322    0.03311 =
         0.03663    0.00412    0.01117    0.00130
N2    3    0.112449    0.677905    0.089202    11.00000    0.01968    0.02468 =
         0.02600    0.00188    0.00729   -0.00294
N3    3    0.552194    0.864697    0.118592    11.00000    0.01867    0.02552 =
         0.02955   -0.00084    0.01075   -0.00230
H3    2    0.658756    0.855181    0.108158    11.00000   -1.20000
C1    1    0.011399    0.779844    0.091931    11.00000    0.02279    0.02604 =
         0.03231    0.00499    0.00833    0.00095
AFIX  43
H1    2    0.022585    0.858860    0.045714    11.00000   -1.20000
AFIX   0
C2    1   -0.075115    0.633023    0.213509    11.00000    0.02337    0.03138 =
         0.02769    0.00228    0.00751   -0.00512
AFIX  43
H2    2   -0.138847    0.588709    0.270378    11.00000   -1.20000
AFIX   0
C3    1    0.057394    0.583147    0.167651    11.00000    0.02485    0.02488 =
         0.02847    0.00301    0.00716   -0.00376
AFIX  43
H3A   2    0.103131    0.499542    0.185968    11.00000   -1.20000
AFIX   0
C4    1    0.249117    0.667494    0.012387    11.00000    0.02259    0.02648 =
         0.02945   -0.00167    0.01161   -0.00326
AFIX  23
H4A   2    0.248001    0.744531   -0.049570    11.00000   -1.20000
H4B   2    0.224760    0.593407   -0.056657    11.00000   -1.20000
AFIX   0
C5    1    0.428746    0.652325    0.124825    11.00000    0.02419    0.02416 =
         0.03505    0.00600    0.01190    0.00202
AFIX  23
H5A   2    0.423609    0.584099    0.197479    11.00000   -1.20000
H5B   2    0.512065    0.625425    0.069176    11.00000   -1.20000
AFIX   0
C6    1    0.496262    0.772645    0.212544    11.00000    0.02240    0.03280 =
         0.02561    0.00432    0.00873   -0.00119
AFIX  23
H6A   2    0.403221    0.810319    0.250420    11.00000   -1.20000
H6B   2    0.595450    0.751350    0.301189    11.00000   -1.20000
AFIX   0
C7    1    0.454455    0.960224    0.047594    11.00000    0.02100    0.02268 =
         0.02637   -0.00608    0.00968   -0.00373
HKLF 4




REM  moc148 in P21/c #14
REM wR2 = 0.1011, GooF = S = 1.076, Restrained GooF = 1.076 for all data
REM R1 = 0.0383 for 1321 Fo > 4sig(Fo) and 0.0553 for all 1701 data
REM 104 parameters refined using 0 restraints

END

WGHT      0.0401      0.1440

REM Highest difference peak  0.276,  deepest hole -0.226,  1-sigma level  0.042
Q1    1   0.3350  0.6613  0.0760  11.00000  0.05    0.28
Q2    1   0.0774  0.6216  0.1131  11.00000  0.05    0.21
Q3    1   0.5220  0.8130  0.1644  11.00000  0.05    0.20
Q4    1  -0.0407  0.5969  0.1333  11.00000  0.05    0.20
Q5    1  -0.0927  0.6910  0.1769  11.00000  0.05    0.18
Q6    1  -0.1635  0.8534  0.1702  11.00000  0.05    0.15
Q7    1   0.0638  0.5483  0.1540  11.00000  0.05    0.14
Q8    1   0.4698  0.8741  0.0379  11.00000  0.05    0.14
Q9    1   0.4413  0.7224  0.1694  11.00000  0.05    0.14
Q10   1   0.0377  0.6304  0.2388  11.00000  0.05    0.14
Q11   1   0.5014  1.0196  0.0207  11.00000  0.05    0.13
Q12   1   0.4415  0.8477  0.2549  11.00000  0.05    0.13
Q13   1  -0.2200  0.7570  0.2057  11.00000  0.05    0.13
Q14   1   0.4216  0.5602  0.1451  11.00000  0.05    0.13
Q15   1   0.0256  0.7057  0.0458  11.00000  0.05    0.13
Q16   1   0.3996  1.0036  0.1139  11.00000  0.05    0.13
Q17   1  -0.0982  0.7596  0.0777  11.00000  0.05    0.13
Q18   1   0.3766  0.8228 -0.1451  11.00000  0.05    0.12
Q19   1   0.6052  0.9468  0.2014  11.00000  0.05    0.12
Q20   1   0.1184  0.4731  0.1386  11.00000  0.05    0.12
;
_shelx_res_checksum              80912
